If pressed for my desert island movie genre, my answer would always be the heist film. The best ones are infinitely rewatchable, with each subsequent viewing revealing how well structured they are with every detail building toward the success of the big con. There’s a sense of wonder, marveling at the (anti)heroes and the filmmakers alike for pulling off something so audacious. When the genre leans into comedy, rather than drama or thriller, it’s all the more fun.
This weekend marks the release of The Hustle, an updated, gender-swapped version of Dirty Rotten Scoundrels starring Anne Hathaway and Rebel Wilson in the roles originated by Michael Caine and Steve Martin. In addition to that ’80s favorite, here are other heist comedies that film fans can watch – and rewatch on an isolated isle if need be – to catch every twist, turn, and joke.
1. Dirty Rotten Scoundrels (1988)
Michael Caine and Steve Martin are rival con artists in this delightful remake of the 1964 David Niven-Marlon Brando film Bedtime Story. Caine is Lawrence Jamieson, a British high-class, big-con expert who takes small-time American goof Martin’s Freddy Benson under his wing as his student – and almost immediately regrets it. The small French Riviera town is the ideal setting to fleece rich, too-trusting women, but it isn’t big enough for the two of them. When innocent heiress Janet Colgate (Glenne Headly) arrives, they compete to be the first to take her money. Directed by Frank Oz, Dirty Rotten Scoundrels plays Caine and Martin’s strengths well off one another, giving Caine the opportunity to work magic with accents and wit, while Martin displays his limber brand of physical comedy. But don’t overlook Headly as their mark; her sweetness contrasts well with the some of the film’s meaner aspects, creating a fine balance.
2. Ocean’s Eleven (2001)
The only team cooler than the Rat Pack in the original 1960 Ocean’s 11 is the group of thieves in Steven Soderbergh’s slick, stylish remake. After working together on another great heist film (though a more serious one) in Out of Sight, the director reteams here with George Clooney, who stars as Danny Ocean. But taking millions from a Las Vegas casino isn’t a one-man job; it requires 11 people’s talents, including acrobatics, explosives, and pickpocketing. For Ocean’s Eleven, Soderbergh assembles a stellar cast, including Julia Roberts, Brad Pitt, Matt Damon, Don Cheadle, Bernie Mac, Andy Garcia, Casey Affleck, Carl Reiner, and more, and the fun they had making this fizzy film is infectious for the audience. The sequels, Ocean’s Twelve and Ocean’s Thirteen, are better than you remember, and the all-female Ocean’s Eight may be a blast, but nothing tops the original for pure energy and glamour.
3. A Fish Called Wanda (1988)
There’s a caper at the heart of this comedy, complete with diamonds that need to be stolen (after already being stolen once), but no one talks about the heist when they’re discussing A Fish Called Wanda. Instead, it’s the quartet of perfect comic performances that drive this equally perfect film from director Charles Crichton. Jamie Lee Curtis stars as Wanda, a con artist who is far more than a gangster’s moll, though she’ll do anything – and anyone – to get her gangster boyfriend’s jewels. Kevin Kline won an Oscar for playing Otto, Wanda’s boyfriend and the gangster’s henchman who isn’t nearly as smart as he thinks he is. In addition to writing the script, John Cleese is Archie Leach, the gangster’s lawyer and most recent target of Wanda’s seduction. And finally, Michael Palin is hapless hitman Ken, who is equally tormented by Otto and by his own inability to murder an old lady. British and American humor are at their peak here in a film that’s equal parts smart and silly.
4. Logan Lucky (2017)
Steven Soderbergh can’t resist making a cheeky nod to his own Ocean’s Eleven with this underrated gem, but he still created something that feels entirely fresh. Instead of swank Las Vegas, West Virginia is the setting for Logan Lucky, and the director trades in ‘00s muse George Clooney for his favorite this decade: Channing Tatum. Here he stars alongside Adam Driver as a pair of brothers who plan to steal millions from a NASCAR race in nearby North Carolina, with help from their sister (Riley Keough) and a trio of brothers (Daniel Craig, Jack Quaid, and Brian Gleeson). Logan Lucky only made off with $30 million at the U.S. box office, but it deserved a much larger haul. Soderbergh’s film is purely entertaining while being oddly good-hearted for a movie about a multi-million-dollar crime in the making.
5. The Sting (1973)
Four years after the Oscar-winning success of Butch Cassidy and the Sundance Kid, Paul Newman and Robert Redford reunite with director George Roy Hill for this film that somehow tops their previous outing together. Here Redford stars as Johnny Hooker, a grifter in Depression-era Chicago whose partner is killed after stealing from the wrong man, Doyle Lonnegan (Robert Shaw), leaving Hooker searching for revenge. He recruits ace con man Henry Gondorff (Newman) and the two set up an elaborate scheme to take down Lonnegan. Newman and Redford have a vibrant chemistry together that matches anything they had with their leading ladies over the years, with each interaction between them filled with sly humor. An all-time great, The Sting pulls one over on the audience with twist after twist, but it never leaves us feeling duped, only making us like it all the more.
6. The Lavender Hill Mob (1951)
Well before A Fish Called Wanda, director Charles Crichton made this sprightly black-and-white caper film. Alec Guinness stars as fastidious, mild-mannered bank clerk Holland, whose job involves overseeing the transport of gold bullion. After decades of low pay and no recognition, he decides to steal a million pounds of gold with a group of criminals who melt the precious metal down into Eiffel Tower paperweights to be smuggled out of England. The fun really begins post-heist when Holland and co. try to recover the Parisian souvenirs, giving Crichton’s innovative direction a chance to shine. Clocking in at just 80 minutes, The Lavender Hill Mob is as fast-moving as a getaway car and features a blink-and-you’ll-miss-it early appearance from Audrey Hepburn in its opening scene. If this film is your speed, be sure to also see another Guinness heist movie from Ealing Studios, 1955 classic The Ladykillers.
7. The Old Man & the Gun (2018)
Most heist films exude cool, but The Old Man & the Gun is pure warmth thanks to the enduring charm of its lead. Robert Redford was 80 years old while making this jazz-inflected crime comedy from writer-director David Lowery, but he still makes the audience blush and giggle through the screen with every smile. The Old Man & the Gun smartly trades on not only Redford’s current charisma but also his previous roles in films like The Sting and Butch Cassidy and the Sundance Kid. Here he plays real-life polite, charming gentleman – and bank robber – Forrest Tucker, who stole money not out of greed, but out of the pure joy of it. Redford said this would be his last film (and then regretted the statement), but if it’s his final lead role, what a fine, fitting end to the career of one of Hollywood’s greatest stars.
The Hustle is in theaters this weekend. Get your tickets now!
